Taking the Lead: Difficult Conversations 101

In Taking the Lead, Law Practice Editorial Board member
Karen MacKay together with guest authors, tackle the ins and outs of running a law firm,
providing expert guidance that every managing partner can use.

Had any tough conversations lately?

It's your job to inspire, motivate and align, but it's also your job to hold people accountable and lead by example.

These tasks will require difficult conversations from time to time.

by Karen MacKay, MBA, CHIC
President

Let's set the stage: When preparing for a conversation on sensitive or controversial matters with Sidney, one of your partners, consider the following.

What is your purpose?

Be clear with yourself about what you are setting out to do. Are you holding up a mirror to raise awareness? Are you calling Sidney out on repeated unacceptable behavior or are you presenting an ultimatum and asking him to perform better? Your purpose will be reflected in your opening line. “I need to give you some feedback. Is this a good time?” is appropriate when your purpose is to raise awareness, but not so when you’ve had it up to here and continued behavior from your partner will erode the firm’s values and culture.

What do you hope to accomplish? What is your end game? Every situation will be different. Do you want to understand what is driving Sidney? You might want to understand what is triggering behavior that is not typical of this partner. You may be reaching out to help a troubled colleague or drawing a line in the sand regarding behavior you will no longer tolerate. Your call, but be clear with yourself.

What is your ideal outcome?

Your desired outcome likely has something to do with where you are along a path of accountability. Is this your first conversation about this issue or is it about to be your last? Do you want to raise awareness; get an explanation? Or is it decision time and Sidney needs to change or go?

What are your assumptions?

Assumptions can help you gather new information and guide the agenda. They can help you understand emotions, fears and biases. Consider your own assumptions going into the conversation. You can guess about Sidney’s assumptions, but you won’t know until you’re into the conversation.

Which of your “buttons” are being pushed?

We all have buttons—they were installed early. Your mother can push them because she likely installed them; buttons such as work ethic, integrity, respect, or my personal favorite, “If you haven’t got something nice to say, don’t say anything at all.” Our buttons are connected to our values. Our values guide our behavior. Collective behavior creates the culture of the firm. If Sidney is aligned with the culture of the firm, you will question your place in it. If Sidney’s behavior is contrary to the culture of the firm where you have likely spent your career, what are you going to do about it? With leadership comes responsibility. Not only do you set a personal example, it is your job to hold your partners accountable for the example they set.

What are your needs and fears?

We all have needs. We all have fears. Leaders who need to be liked (or loved) will have a tough time with a difficult conversation. We all have a different ways of dealing with conflict. Some of us avoid it at all cost. Others compete to win—at all cost. Some of us, perhaps because we were middle children, look for compromise. The truth is that compromise can often be lose-lose. Do you need to win or do a deal? Are you afraid of eroding your firm’s values or that you’ll lose the respect of Sidney or of everyone else? When the going gets tough, what do you need at your core?

How are you contributing to the situation? Are you an enabler? Are you the guardian of the firm’s core values?

Last word

The leadership competency that is most challenging in every firm that I’ve been privileged to serve is conflict management. Every difficult conversation is a test.

You will sit up a little straighter and stand a little taller when you handle a difficult conversation well. You will earn political capital and the respect of your colleagues at all levels in the firm when you handle a difficult conversation with skill and integrity. Trusted leaders can manage conflict, encourage debate and align colleagues. Handle it well (or blow it) and you will set a personal example. That’s leadership. Nobody said it would be easy.